Donald Trump stands to personally profit from the legislative agenda he is expected to push in his first 100 days, raising questions about whether he can separate his financial interest from his public office without totally cutting ties from his business empire.

The top items on the president-elect’s policy checklist — from rewriting the tax code to scrapping Wall Street regulations to repealing Obamacare — have for years been Republican orthodoxy. But Trump could see a direct benefit to muscling through broad tax cuts and eliminating regulations: billions of dollars in new savings for him and his family and fresh revenue for his business portfolio, according to a POLITICO analysis of Trump’s public statements and financial disclosures and interviews with tax experts.

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“It’s kind of unprecedented that a president would be proposing tax and regulatory changes that have such a significant benefit to him and his family and presumably his business partners as well,” said Leslie Samuels, a tax attorney and former senior Clinton administration Treasury official. “It’s a combination of changes that have a potential for a material benefit of a large magnitude.”

The Republican tax code overhaul is expected to include across-the-board tax cuts, including one to the top business tax rate that would allow Trump’s companies to keep a greater share of their profits. Beyond the rate reduction, Trump could also benefit from several other provisions likely to be part of the GOP tax reform package, such as a proposed exemption on foreign income generated from overseas sales, from certain business interest deductions on debt-financed projects that are widely favored by real estate developers and from provisions allowing small-business owners to tap into a lower 15 percent rate when they file using their personal-income returns.

And Trump’s family stands to significantly benefit — an estimated savings of $4 billion or more if the president-elect’s personal wealth is “in excess of $10 billion” as he has claimed — from a repeal of the estate tax, a tax on inheritance that applies to only a small number of the country’s wealthiest families.

Trump is promising his administration will deliver ethics safeguards to alleviate concerns about conflicts of interest between public policy and private profit, and his team says he could announce that plan as early as next week after he pushed back a promised announcement in December. His critics say an effective ethics safeguard requires him to divest entirely from his businesses and put his liquidated assets in a blind trust, but to date Trump has been hesitant to cut all ties with his business operations.

“The real challenge with Trump is he’s got so much at stake,” said Steven Rosenthal, a senior fellow at the Urban-Brookings Tax Policy Center. “It’s really a question of degree to a large measure.”

In delaying the December release, Trump promised his company would do “no new deals” while he is in office and that the business would be run by his two adult sons: Donald Trump Jr. and Eric Trump. But even if Trump is not actively involved in running his business, simply executing the big-ticket items he and his GOP colleagues have promised would bolster his bottom line.

That’s not illegal, as a key conflict of interest law from 1989 specifically exempts the president. It is, however, an awkward reality for the president to be making money off his own policies. And as Trump and GOP leaders set their agenda in motion, Democrats plan to highlight the ethical hazards as part of a broader strategy to paint the new president as looking out for himself and his wealthy associates at the expense of the middle-class workers he promised to champion.

“To say the least it’s a very rich field,” said Rep. Joseph Crowley (D-N.Y.), a senior member of the party’s leadership team. “I think there’s unfortunately too many opportunities to call into question the conflicts of interest that will be laid before the president-elect when he takes office.”

Trump’s potential conflicts of interest aren’t limited to tax reform. He stands to benefit from planned GOP changes to the 2010 Dodd-Frank financial reform law, namely looser banking standards that can facilitate faster lending for commercial real estate. Democrats say such a legislative move would create conflict questions for the president-elect because it would drive up property prices and benefit real estate developers like Trump and his son-in-law, Jared Kushner.

“I don’t think it’s a complicated connection at all,” said Norm Eisen, former chief Obama White House ethics lawyer now chairman of the liberal government watchdog group Citizens for Responsibility and Ethics in Washington. “He’s a real estate developer first and foremost and real estate developers live on leverage. That’s provided by banks and so of course anything he’s doing to benefit a bank is going to call the bias of his decision making into question.”

Republicans concede Trump should be ready to face critics about his personal motivations as he pursues changes to the 2010 Dodd-Frank law, especially in the wake of hiring an economic team that includes several veterans from Goldman Sachs, the New York-based finance powerhouse widely blamed for playing a role in the economic crisis.

“There’s going to be all sorts of accusations that any reform of Dodd-Frank is self-dealing. They’re just going to have to face up to that,” said Doug Holtz-Eakin, the former head of the Congressional Budget Office and John McCain 2008 economic adviser.

Republican plans for dismantling Obamacare also stand to lighten the tax load for Trump, as well as other rich individuals. The law imposes several high-end Medicare taxes on the wealthiest Americans, including a 0.9 percent tax on “earned income” and a 3.8 percent surtax on capital gains, dividends and passive income generated from things like rental property, bank interest and patent royalties.

While a full accounting of Trump’s tax liability from Obamacare is uncertain because the president-elect runs a private company and the only public information on his finances has come through his bare-bones reporting via federal campaign disclosure forms, the data appear to show the president-elect could save at least $6.7 million if the two Medicare taxes were nixed. Trump reported more than $557 million in income in his May 2016 filing to the Federal Election Commission, meaning he’d save about $5 million if the 0.9 percent tax was repealed, according to POLITICO’s analysis. And two former George H.W. Bush tax officials, including former IRS commissioner Fred Goldberg, estimated in a recent New York Times op-ed that Trump had passive investment income of at least $43 million, making him liable for $1.7 million in Medicare taxes via Obamacare’s 3.8 percent surtax.

Trump’s transition office did not respond to a request for comment about the political challenges ahead for his legislative agenda, but the next president’s defenders see his business experience as an asset. They also say that it shouldn’t be a surprise that his businesses stands to benefit from the GOP agenda, as the party hopes its agenda will help all businesses.

“I don’t think the Republican Congress will look for ways to make Donald Trump an unsuccessful businessman,” Rep. Kevin Cramer, a North Dakota Republican who was among the earliest of Trump’s Capitol Hill supporters, told POLITICO. “We’re not going to punish him because he won the presidency.”

Trump’s legislative and policy agenda may not be all good news for his bottom line. Scientists warn that his calls to unravel Obama-era climate change policies will exacerbate sea level rise and further threaten some of his coastal properties and golf courses. His rhetoric surrounding building a wall on the U.S.-Mexico border and banning Muslims has the potential to damage his company’s brand. And by repealing Obamacare, Trump also could undercut the very marketplace that helped launch Oscar Insurance, a tech startup co-founded by Ivanka Trump’s brother-in-law Joshua Kushner and funded in part by Trump supporter Peter Thiel.

Still, Democrats believe that pointing out Trump’s potential personal gains will be a complement to their broader strategy: painting the new regime’s policies as a betrayal of the working class in favor of the wealthiest Americans.

“Trump is sort of a proxy and key stand-in reminder about who the Republican policies are going to be helping and who they’re going to be hurting,” said a senior Senate Democratic aide working on the 2017 legislative opposition strategy.

Massachusetts Rep. Richard Neal, the Democratic ranking member of the powerful Ways and Means Committee, said he was reluctant to begin criticizing Trump over the potential benefits he’ll receive from a 2017 tax reform package until more details of the legislation emerge.

But he added, “We can state the obvious. The president-elect indicated during the course of the campaign there were lots of loopholes that only he knew how to fix. That’s a pretty bold statement.”

Democrats lack the votes to block much of Trump’s agenda, particularly changes Republicans plan to make via budget procedures that require just 51 votes to move through the Senate. So they’re planning to use the GOP effort largely as a campaign and messaging strategy, hoping to punish the president and take back power in upcoming elections.

They’ve already introduced legislation demanding Trump cut ties with his business, and they’re eyeballing amendments to top Republican-backed bills in 2017 that would highlight how the their agenda benefits Trump personally.

Democrats also plan to continually demand oversight hearings on Trump’s conflicts of interest, and they’re saying they’ll hold more of their own unofficial “shadow hearings” if they can’t get their cross-aisle colleagues to play ball. They’re also threatening to obstruct confirmation of Cabinet nominees to highlight Trump’s own potential conflicts of interest and those of his incoming administration, several senior Democratic lawmakers, operatives and congressional aides told POLITICO.

“The bottom line is we don’t run the floor. We don’t run the committees,” Crowley said. “As they push through their bills what we will use is every opportunity and every legislative means available to us to expose what they’re doing and what they’re trying to do and the conflicts of interest that exist, not only for the president but Republicans who defend them as well.”

But Democrats also recognize that their new efforts to sidetrack Trump’s presidency — by highlighting his potential personal financial gains —might be no more successful than their earlier ones to sink his campaign. And while conflict of interest concerns dogged Trump during the campaign, they didn’t stop him from winning the Electoral College.

“After the last year,” said longtime Democratic operative Jim Manley, “it’s going to be interesting to see whether the American people care or not.”